Tax season strikes certain weariness into small business owners. Some say its fear, but I think it is more likely that we dread the time sink of preparing our own taxes or working with a CPA or accountant.

Enter Shoeboxed – a receipt capture and tracking service that lets you improve how you approach expenses and how you organize receipts.

Shoeboxed Review

Shoeboxed is one of the market leaders in receipt and expense management for small business owners. The concept is you can snap a simple photo with your camera or smartphone and instantly upload the receipt to the web-based service. The goal is to get that receipt out of your “shoebox.” As you upload each receipt, the service asks you how to categorize the item and creates an expense report on the fly.

There’s so much to like with this service. It really is a time-saver and a valuable service. How many receipts do you have piled up on a desktop or in a drawer or envelope? I save all of mine until tax season and then manually tally them up. Silly really, when this could save me so much time, effort, and a bit of anxiety getting all my stuff in order each year. Paid plans start at $9.95 per month.

A few minutes after uploading my first receipt screenshot, I received an email confirming that it would be processed within one business day. Your receipts will process more quickly on the paid plans, I’m sure, but you receive 50 free receipts on the forever free plan if you can deal with the slight time lag.

If you upload a bunch of receipts, you will only receive one email saying “submission received.” If the receipt is invalid, not readable, or otherwise unacceptable, the email states that they will notify you separately, otherwise, assume all is well.

What I Really Like

A confirmation email. Shoeboxed emails you almost immediately that your receipt is accepted and pending. The forever free account has a slight processing delay of up to one business day, but I found it was often less.

When you change a category, the system asks you if you want to do this for all similar receipts, as in this example, for Starbucks receipts. It will go back and change existing ones, plus it will not allow you to choose that category again (if you mark that option) in the future.

Bulk receipt envelopes. On the paid plans, you can simply mail Shoeboxed that stack of receipts you have been saving all year in what they refer to as a “Magic Envelope.” Pretty handy at this time of year, or a bit earlier.

What I Would Like to See:

An end to the misleading signup process. Let me be very clear: Shoeboxed offers a valuable service, but in the process of signing up you may click the wrong button and move into a paid option. The landing page shows a super, super simple signup – enter your email for the “forever free” plan. But then it takes you to a full signup page where you have to navigate options and hunt for that “forever free” option that appears at the very bottom of the page. I’m sure you could opt out of the paid plan easily enough, but I prefer to see all options more clearly than one buried at the bottom.

A direct link for Android mobile devices. The mobile link on the main site takes you to the iOS version in iTunes. You can find it by searching in Google Play and install it from there.